Abedin worked for Clinton while she was secretary of state in the Obama administration. The Democratic frontrunner is under fire from Republicans over her use of a private email server while in that job.

Trump, who was speaking to more than a thousand people at the estate of car dealer Ernie Boch, said that while Abedin worked at the State Department she had been “getting classified information” while married to a man he described “a perv”, “a sleazebag” and just “a bad guy”.

Trump also opined that Abedin “is probably desperately in love with [Weiner] … because why else would she marry that guy?”

Weiner resigned from Congress in 2011 , after he accidentally tweeted a sexually suggestive picture that he meant to share with an internet acquaintance. He initially claimed his account had been hacked.

In 2013, he launched an unsuccessful attempt to be elected mayor of New York City. The campaign collapsed when it was revealed that he had continued to send explicit photographs to women on the internet, and had used the name “ Carlos Danger ”. In July, it was reported that he had taken a post with a firm specialising in public relations.

Trump has faced criticism from other Republicans about his past donations to and closeness with Clinton and her husband, former president Bill Clinton. He did not mention on Friday that in 2010, he donated $2,000 to the congressional election campaign of Anthony Weiner.

Slipping into a double negative, Trump said there was a less than “5% chance that’s she’s not telling Anthony Weiner now of a public relations firm what the hell is coming across” her desk.

In remarks that may contribute to debate about Trump’s alleged sexism, which ignited when he appeared to suggest that Kelly had asked him tough questions in the first Republican debate because she had been menstruating, the candidate then asked the crowd: “Are there any women in this room in love with their husbands who wouldn’t be telling them everything?”

Responding to a woman who apparently shouted “I wouldn’t”, he said: “She said, ‘I wouldn’t but I’m in love’.”

He then insisted: “No, you will.”

The crowd laughed as Trump said this was a “very sad situation”.

Abedin, whose name Trump incorrectly pronounced as “Oohma”, has been a top aide to Clinton for more than a decade. She has regularly been the subject of attention from Republicans and the press.

She has recently come under scrutiny from the Republican senator Chuck Grassley, for having held posts in the private sector while working at the State Department. This was not mentioned by Trump.

In a statement to the Guardian, Clinton campaign spokesman Nick Merrill said: “Donald Trump has spent the summer saying offensive things about women, but there is no place for patently false, personal attacks towards a staff member.

“He should be ashamed of himself, and others in his own party should take a moment to stand up to him and draw the line for once.